Reaction #1702064

Reaction equation

5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene

dichloromethane

aluminum chloride

propionyl chloride

→

5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted by ethyl acetate
2. 2
   WashThe organic layer was washed by water
3. 3
   Dryinga saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe crude product was purified by silica gel column chromatography

Procedure

To 5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene (204 mg, 1.00 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (148 mg, 1.12 mmol), and propionyl chloride (101.7 mg, 1.10 mmol) followed by stirring at 60° C. for 16 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using hexane/ethyl acetate (20/1) as an elution solvent. The yield was 117 mg (45%).

Source